2,6-DICHLORO-1,4-BENZOQUINONE

2,6-DICHLORO-1,4-BENZOQUINONE Basic information
Product Name:2,6-DICHLORO-1,4-BENZOQUINONE
Synonyms:LABOTEST-BB LT00159342;2,6-DICHLORO-1,4-BENZOQUINONE;2,6-DICHLORO-P-QUINONE;2,6-DICHLORO-P-BENZOQUINONE;2,6-Dichloquinone;2,6-Dichloro-2,5-cyclohexa-diene-1,4-dione;2,6-dichloro-2,5-cyclohexadiene-1,4-dione;2,6-Dichlorobenzo-1,4-quinone
CAS:697-91-6
MF:C6H2Cl2O2
MW:176.98
EINECS:211-810-0
Product Categories:Anthraquinones, Hydroquinones and Quinones;Benzoquinones;C3 to C6;Carbonyl Compounds;Ketones
Mol File:697-91-6.mol
2,6-DICHLORO-1,4-BENZOQUINONE Structure
2,6-DICHLORO-1,4-BENZOQUINONE Chemical Properties
Melting point 122-124 °C(lit.)
Boiling point 251.81°C (rough estimate)
density 1.5138 (rough estimate)
refractive index 1.4595 (estimate)
storage temp. Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
color Dark Yellow
Water Solubility Insoluble in water. Solubility in methanol (almost transparency).
Stability:Hygroscopic
CAS DataBase Reference697-91-6(CAS DataBase Reference)
EPA Substance Registry System2,5-Cyclohexadiene-1,4-dione, 2,6-dichloro- (697-91-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DK4000000
TSCA Yes
HS Code 2914698090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
2,6-DICHLORO-1,4-BENZOQUINONE Usage And Synthesis
Chemical Propertiesyellow crystalline powder
Uses2,6-Dichloro-1,4-benzoquinone is the suitable reagent used to in a study to evaluate the diffusion coefficients (D) for a family of quinones, nitroaromatics, ferrocenes and aromatic hydrocarbon compounds, in acetonitrile by single potential step chronoamperometry.1 It may be used in the preparation of 2,3,5-Trichloro-1,4-dihydroquinone, 2,3,5-trichloro-1,4-benzoquinone and 2,6-Dichloro-1,4-dihydroquinone.
DefinitionChEBI: 2,6-dichlorobenzoquinone is a member of the class of 1,4-benzoquinones that is p-benzoquinone in which the hydrogens at positions 2 and 6 have been replaced by chlorines. A highly toxic and carcinogenic disinfection by-product found in drinking water. It has a role as a carcinogenic agent and a poison. It is a member of 1,4-benzoquinones and an organochlorine compound.
General Description2,6-Dichloro-1,4-benzoquinone (DCBQ, 2,6-DCBQ) is a halobenzoquinone. Halobenzoquinones are disinfection byproducts (DBPs) found in drinking water. They are capable of producing reactive oxygen species and causing oxidative damage to proteins and DNA in T24 human bladder carcinoma cells. UV-induced transformation of DCBQ in drinking water has been reported. Detection of DCBQ in drinking water by liquid chromatography-ESI tandem mass spectrometry has been reported.
Purification MethodsRecrystallise the quinone from pet ether (b 60-70o). It sublimes at 41o/17.6. [Carlson & Miller J Am Chem Soc 107 479 1985, Beilstein 7 II 580. 7 III 3376.]
Triethylamine Vinyl acetate 2,3,5-TRICHLORO-1,4-BENZOQUINONE 2-CHLORO-2-BUTENE 1,3-Dichloropropane 1,3-Dichloroacetone 2,5-Diamino-3,6-dichloro-1,4-benzoquinone N,N'-Dicyano-2,5-dichloro-1,4-benzoquinone diimine 2,6-DICHLORO-1,4-BENZOQUINONE 2-CHLORO-1,4-BENZOQUINONE 2,3-Dichloro-1,4-benzoquinone Chloranil 2,5-DICHLORO-1,4-BENZOQUINONE 4,5-Dichloro-1,2-benzoquinone 1,4-Benzoquinone Chloranilic acid

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